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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2012-09-11 20:51:52 UTC
Update Date2019-07-23 06:19:40 UTC
HMDB IDHMDB0035841
Secondary Accession Numbers
  • HMDB35841
Metabolite Identification
Common NameCitronellal
DescriptionCitronellal, also known as beta-citronellal or 2,3-dihydrocitral, belongs to the class of organic compounds known as acyclic monoterpenoids. These are monoterpenes that do not contain a cycle. Citronellal is an extremely weak basic (essentially neutral) compound (based on its pKa).
Structure
Data?1563862780
Synonyms
ValueSource
2,3-DihydrocitralChEBI
3,7-Dimethyl-6-octen-1-alChEBI
3,7-Dimethyl-6-octenalChEBI
beta-CitronellalChEBI
b-CitronellalGenerator
Β-citronellalGenerator
3,7-Dimethyloct-6-enalHMDB
beta -CitronellalHMDB
FEMA 2307HMDB
RhodinalHMDB
Citronellal, (+-)-isomerHMDB
Citronellal, (S)-isomerHMDB
Citronellal, (R)-isomerHMDB
Chemical FormulaC10H18O
Average Molecular Weight154.253
Monoisotopic Molecular Weight154.1357652
IUPAC Name3,7-dimethyloct-6-enal
Traditional Namecitronella
CAS Registry Number106-23-0
SMILES
CC(CCC=C(C)C)CC=O
InChI Identifier
InChI=1S/C10H18O/c1-9(2)5-4-6-10(3)7-8-11/h5,8,10H,4,6-7H2,1-3H3
InChI KeyNEHNMFOYXAPHSD-UHFFFAOYSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as acyclic monoterpenoids. These are monoterpenes that do not contain a cycle.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassPrenol lipids
Sub ClassMonoterpenoids
Direct ParentAcyclic monoterpenoids
Alternative Parents
Substituents
  • Acyclic monoterpenoid
  • Medium-chain aldehyde
  • Alpha-hydrogen aldehyde
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Aldehyde
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
Disposition

Route of exposure:

Biological location:

Source:

Process

Naturally occurring process:

Role

Industrial application:

Biological role:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.36 g/LALOGPS
logP3.25ALOGPS
logP2.71ChemAxon
logS-2.6ALOGPS
pKa (Strongest Acidic)18.32ChemAxon
pKa (Strongest Basic)-7ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area17.07 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity49.3 m³·mol⁻¹ChemAxon
Polarizability19.18 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-066v-9200000000-145d8f7001c4ce77fa8cSpectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-066u-9100000000-95b49c5f5088a3eddc72Spectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-066v-9200000000-145d8f7001c4ce77fa8cSpectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-066u-9100000000-95b49c5f5088a3eddc72Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-000x-9400000000-61094362cba6ad2562d7Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a4i-1900000000-facaeed6253aef58db1eSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0aor-9700000000-246e147d68730886b936Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0ldl-9000000000-a497aaf732131b397f9bSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-0900000000-804231e21b402460f30fSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0udi-2900000000-e11d5a0124399999066aSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-9300000000-55b14a46099707c2eeb9Spectrum
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB019943
KNApSAcK IDC00035823
Chemspider ID7506
KEGG Compound IDC17384
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkCitronellal
METLIN IDNot Available
PubChem Compound7794
PDB IDNot Available
ChEBI ID47856
Food Biomarker OntologyNot Available
VMH IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Download (PDF)
General References
  1. Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9. [PubMed:11413487 ]
  2. Watson AD: Thematic review series: systems biology approaches to metabolic and cardiovascular disorders. Lipidomics: a global approach to lipid analysis in biological systems. J Lipid Res. 2006 Oct;47(10):2101-11. Epub 2006 Aug 10. [PubMed:16902246 ]
  3. Sethi JK, Vidal-Puig AJ: Thematic review series: adipocyte biology. Adipose tissue function and plasticity orchestrate nutritional adaptation. J Lipid Res. 2007 Jun;48(6):1253-62. Epub 2007 Mar 20. [PubMed:17374880 ]
  4. Lingwood D, Simons K: Lipid rafts as a membrane-organizing principle. Science. 2010 Jan 1;327(5961):46-50. doi: 10.1126/science.1174621. [PubMed:20044567 ]
  5. (). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .
  6. Gunstone, Frank D., John L. Harwood, and Albert J. Dijkstra (2007). The lipid handbook with CD-ROM. CRC Press.